O,S,Se-containing Biginelli products based on cyclic β-ketosulfone and their postfunctionalization

• Kateryna V. Dil and
• Vitalii A. Palchykov

Beilstein J. Org. Chem. 2024, 20, 2143–2151, doi:10.3762/bjoc.20.184

• regioselectivity to give diverse DHPMs in reasonable yields up to 95%. Moreover, an SO2-containing analogue of anticancer drug-candidate enastron (SO2 vs C=O) was obtained by using the here reported method in gram scale. We also demonstrate the reactivity of the Biginelli product in various directions – synthesis

• /9.26→9.75/10.50→10.26/10.85 ppm) and become more equivalent (Δδ = 1.39→0.75→0.59 ppm accordingly). The key signal in the 13C NMR spectra is located in the regions 174.04–174.69 ppm (C=S), 151.44–151.86 ppm (C=O), and 170.15–170.91 ppm (C=Se) accordingly. Utilization of reaction products The Biginelli

• -4,6,7,8-tetrahydro-1H-thiopyrano[3,2-d]pyrimidine-2(3H)-one/thione/selenone 5,5-dioxides and some of their derivatives. Furthermore, this methodology was successfully applied for the synthesis of the SO2-containing analogue of the anticancer drug-candidate enastron (SO2 vs C=O), and we believe a multitude

Factors influencing the performance of organocatalysts immobilised on solid supports: A review

• Zsuzsanna Fehér,
• Dóra Richter,
• Gyula Dargó and
• József Kupai

Beilstein J. Org. Chem. 2024, 20, 2129–2142, doi:10.3762/bjoc.20.183

• more precise stereocontrol of the reaction [128][129][130][131][132]. Therefore, the difference in enantioselectivity values may be attributed to these electronic effects. Ultimately, the most favourable outcomes were achieved with catalyst C30 at 0 °C, with yields reaching up to 84% and enantiomeric

Efficacy of radical reactions of isocyanides with heteroatom radicals in organic synthesis

• Akiya Ogawa and
• Yuki Yamamoto

Beilstein J. Org. Chem. 2024, 20, 2114–2128, doi:10.3762/bjoc.20.182

• perfluoroalkyl radical, as a carbon radical, rather than iodine radical can add to isocyanides to form imidoyl radicals. Then, the iodine atom of RFI can trap the imidoyl radicals to give the corresponding 1,1-adducts (R–N=C(I)–RF) in good yields [25][26]. Radical addition of group 16 compounds to isocyanides In

• ]. In the case of aromatic isocyanides, the 1,1-addition reaction is probably more likely to proceed because the C–N double bond of the 1,1-addition product 4 (R = Ar, E = PhS) is conjugated to the aromatic ring, which stabilizes it compared to the corresponding adduct with aliphatic isocyanides

• lack of geometrical isomerization of the C–N double bond of the dithiolation products [32]. The thioselenation product 6’, an imine derivative, can be converted to a β-lactam derivative by [2 + 2] cycloaddition with ketene generated in situ. For example, thioselenation of RNC (R = (EtO)2P(O)–CH2) gave

From perfluoroalkyl aryl sulfoxides to ortho thioethers

• Yang Li,
• Guillaume Dagousset,
• Emmanuel Magnier and
• Bruce Pégot

Beilstein J. Org. Chem. 2024, 20, 2108–2113, doi:10.3762/bjoc.20.181

• study, many research groups described a strategy for ortho-C–H functionalization of aryl sulfoxides with various nucleophiles via a cascade reaction of interrupted Pummerer reaction/sigmatropic rearrangement (Scheme 1a) [6][7][8][9][10][11]. A large range of nucleophiles, such as phenols [12][13][14][15

• conditions, a significant amount of degradation products was observed and the yield was rather low. The same result was obtained when the reagent was first added at 0 °C and then heated for one hour under microwave irradiation (Table 1, entry 2). To avoid degradation, the temperature was reduced while the

• reaction time was increased with twice the number of equivalents of acetonitrile (−15 °C to rt, for 12 hours, entry 3 in Table 1) without any significant improvement in the yield. As previously reported, the use of an organic base can improve the yield of this reaction [26][38][40][48]. Therefore, we

Computational toolbox for the analysis of protein–glycan interactions

• Ferran Nieto-Fabregat,
• Maria Pia Lenza,
• Angela Marseglia,
• Cristina Di Carluccio,
• Antonio Molinaro,
• Alba Silipo and
• Roberta Marchetti

Beilstein J. Org. Chem. 2024, 20, 2084–2107, doi:10.3762/bjoc.20.180

• of different and particular structures [7][8]. Additionally, glycans can adopt a wide variety of different shapes; five-membered ring sugars can exhibit envelope and twist conformations usually represented on a pseudo-rotational wheel; while six-membered ring structures can adopt chair (C), boat (B

• glycosylation: i) N-glycosylation, where a N-acetylglucosamine (GlcNAc) is linked to the nitrogen atom of an asparagine side chain [28]; ii) O-glycosylation, where a GlcNAc or N-acetylgalactosamine (GalNAc) is linked to the hydroxy group of a serine or threonine residue [29]; iii) C-glycosylation, where a

• on Voronoi tessellation and alpha spheres. It consists of three main programs: Fpocket for pocket identification, Tpocket for benchmarking pocket detection, and Dpocket for collecting pocket descriptor values. Written in C, Fpocket is well-suited for developing new scoring functions and extracting

Cage-like microstructures via sequential Ugi reactions in aqueous emulsions

• Rita S. Alqubelat,
• Yaroslava A. Menzorova and
• Maxim A. Mironov

Beilstein J. Org. Chem. 2024, 20, 2078–2083, doi:10.3762/bjoc.20.179

• , which was monitored through the disappearance of isocyanide in the reaction medium using a color reaction [19]. Then the emulsion was applied to the glass surface and evaporated at a temperature of 50 °C. The resulting samples were analyzed using fluorescence microscopy at a wavelength of 490 nm. After

Multicomponent syntheses of pyrazoles via (3 + 2)-cyclocondensation and (3 + 2)-cycloaddition key steps

• Ignaz Betcke,
• Alissa C. Götzinger,
• Maryna M. Kornet and
• Thomas J. J. Müller

Beilstein J. Org. Chem. 2024, 20, 2024–2077, doi:10.3762/bjoc.20.178

• Ignaz Betcke Alissa C. Gotzinger Maryna M. Kornet Thomas J. J. Muller Heinrich-Heine-Universität Düsseldorf, Math.-Nat. Fakultät, Institut für Organische Chemie und Makromolekulare Chemie, Universitätsstrasse 1, D-40225 Düsseldorf, Germany Zaporizhzhia National University, Faculty of Biology

• is that the reaction with methylhydrazine leads to two different regioisomers. Shen et al. used a concept developed by them for the C-acylation of β-ketoesters for the one-pot synthesis of pyrazoles. SmCl3-catalyzed acylation of these yields the 1,3-diketones 4, and after cyclization with hydrazine

• -pot process can be conducted in various solvents such as in PEG 400 [79], ionic liquids like 1-butyl-3-methylimidazolium hydroxide ((Bim)OH) [80], the nanoionic liquid 1-methylimidazolium trinitrocarbide ([[HMIM]C(NO2)3]) [81], N-methylpyridinium tosylate (NMPYT) [82], or glucose-based strong eutectic

Diastereoselective synthesis of highly substituted cyclohexanones and tetrahydrochromene-4-ones via conjugate addition of curcumins to arylidenemalonates

• Deepa Nair,
• Abhishek Tiwari,
• Banamali Laha and
• Irishi N. N. Namboothiri

Beilstein J. Org. Chem. 2024, 20, 2016–2023, doi:10.3762/bjoc.20.177

• methodology (Table 2). At first, various arylidenemalonates 2 were tested with a phenyl analog of curcumin 1. The reaction of 1a with arylidene malonates 2a–c, bearing weakly electron-withdrawing para-substituents, produced the corresponding double Michael adducts 3a–c, respectively, in good to high yields

• (55–75%) with excellent diastereoselectivity (Table 2, entries 1–3). At the same time, the corresponding triple Michael adducts 4a–c were also formed as minor products (12–36%). There was no reaction with ortho-nitro-substituted arylidenemalonate 2d under the optimized conditions which is attributable

• ). In the next set of experiments, different curcumins were examined while keeping 2a as the model arylidenemalonate (Table 2, entries 9–11). The reaction of p-tolyl and p-bromophenyl analogs of curcumin 1b,c led to the formation of double Michael adducts 3i–j in moderate yields (35–43%) over prolonged

Understanding X-ray-induced isomerisation in photoswitchable surfactant assemblies

• Beatrice E. Jones,
• Camille Blayo,
• Jake L. Greenfield,
• Matthew J. Fuchter,
• Nathan Cowieson and
• Rachel C. Evans

Beilstein J. Org. Chem. 2024, 20, 2005–2015, doi:10.3762/bjoc.20.176

• Beatrice E. Jones Camille Blayo Jake L. Greenfield Matthew J. Fuchter Nathan Cowieson Rachel C. Evans Department of Materials Science & Metallurgy, University of Cambridge, 27 Charles Babbage Road, CB3 0FS, United Kingdom Diamond Light Source, Harwell Science and Innovation Campus, Didcot

• pattern to that of the native, E isomer (Figure 2). Changes occur immediately, after 1 s of X-ray exposure, and saturate after ca. 5 s. The changes are comparable to those observed on Z–E isomerisation induced using blue (460 nm) light or heating to 55 °C but occur at a much faster rate (Figure S2

• the micelle shape of this isomer. The fast rate of the morphology change, in comparison to using blue light or heating to 55 °C, shows rapid rates of Z–E isomerisation from X-ray-induced catalysis, which may be due to the presence of multiple different catalysing species and therefore isomerisation

Harnessing the versatility of hydrazones through electrosynthetic oxidative transformations

• Aurélie Claraz

Beilstein J. Org. Chem. 2024, 20, 1988–2004, doi:10.3762/bjoc.20.175

• readily available hydrazones under mild, safe and oxidant-free reaction conditions. This review presents a comprehensive overview of oxidative electrosynthetic transformations of hydrazones. It includes the construction of azacycles, the C(sp2)−H functionalization of aldehyde-derived hydrazones and the

• access to diazo compounds as either synthetic intermediates or products. A special attention is paid to the reaction mechanism with the aim to encourage further development in this field. Keywords: C–H functionalization; diazo compound; electrosynthesis; hydrazone; nitrogen-containing heterocycle

• -methoxymethylpyrrolidine)hydrazones could be also key intermediates for the asymmetric synthesis of α-substituted aldehydes and ketones [18][19]. Interestingly, depending on the substitution pattern, the C=N bond can feature different electronic properties [20]. For instance, various hydrazones have been employed for the

Allostreptopyrroles A–E, β-alkylpyrrole derivatives from an actinomycete Allostreptomyces sp. RD068384

• Marwa Elsbaey,
• Naoya Oku,
• Mohamed S. A. Abdel-Mottaleb and
• Yasuhiro Igarashi

Beilstein J. Org. Chem. 2024, 20, 1981–1987, doi:10.3762/bjoc.20.174

• ; HRESITOFMS (m/z): [M – H]– calcd for C15H22NO4, 280.1554; found, 280.1550. Allostreptopyrrole B (2): greenish yellow amorphous solid; +15 (c 0.10, MeOH); UV (MeOH) λmax, nm (log ε): 235 (3.87), 273 sh (3.49); IR (ATR) νmax: 3263, 2964, 2925, 2854, 1658, 1556, 1417 cm−1; 1H and 13C NMR data, see Table 2

• ; HRESITOFMS (m/z): [M – H]– calcd for C15H22NO4, 280.1554; found, 280.1554. Allostreptopyrrole C (3): greenish yellow amorphous solid; −6.1 (c 0.10, MeOH); UV (MeOH) λmax, nm (log ε): 235 (3.82), 276 sh (3.46); IR (ATR) νmax: 3265, 2925, 2856, 1657, 1555, 1417 cm−1; 1H and 13C NMR data, see Table 2

• , 332.1832; found, 332.1838. Methylation of 1 Allostreptopyrrole A (1, 2.0 mg, 0.007 mmol) and K2CO3 (4.4 mg, 0.032 mmol) were stirred in dry DMF (0.5 mL) at 50 °C for 10 min. Methyl iodide (19 μL, 0.32 mmol) was added and the mixture was stirred at this temperature for 12 h [29]. Reaction completion was

Development of a flow photochemical process for a π-Lewis acidic metal-catalyzed cyclization/radical addition sequence: in situ-generated 2-benzopyrylium as photoredox catalyst and reactive intermediate

• Masahiro Terada,
• Zen Iwasaki,
• Ryohei Yazaki,
• Shigenobu Umemiya and
• Jun Kikuchi

Beilstein J. Org. Chem. 2024, 20, 1973–1980, doi:10.3762/bjoc.20.173

• , initiating further radical reactions through the formation of radical cations B. Nucleophilic arylmethyl radicals C, which are generated from radical cations B by desilylation, undergo an addition reaction with 2-benzopyrylium intermediates A, giving rise to the corresponding radical cation. Catalytic cycle

• 2a, and 0.5 mmol (5 equiv) of TFA under light irradiation (blue LED: λmax = 448 nm) at 50 °C for 1 h in 1 mL (total volume) of 1,2-DCE] [55] with a flow rate of 3 mL/h (light irradiation time: 20 min in the flow reaction, 1 h in the batch reaction). As shown in Table 1, product 3a was obtained in

• moderate yield (entry 1: 42%, cf. batch reaction: 76%). Lowering the reaction temperature to 25 °C reduced the yield (Table 1, entry 2: 35%), but decreasing the amount of the phosphine ligand from 20 mol % to 5 mol % markedly improved the yield (Table 1, entry 3: 53%). Even when the flow rate was increased

Radical reactivity of antiaromatic Ni(II) norcorroles with azo radical initiators

• Siham Asyiqin Shafie,
• Ryo Nozawa,
• Hideaki Takano and
• Hiroshi Shinokubo

Beilstein J. Org. Chem. 2024, 20, 1967–1972, doi:10.3762/bjoc.20.172

• the electrophile [16][17][18]. In addition, C–C double bonds of the norcorrole skeleton outside the π-delocalization pathway exhibit a reactivity similar to an alkene to afford hydrogenated norcorroles by hydrogenation [19] or reduction with hydrazine [20] and [3 + 2]-cycloadducts with 1,3-dipoles [21

• core. For the byproducts, 3a would be generated through the quenching of radical I with a hydrogen atom source. Bisdipyrrin 4a could be formed through the ring-opening reaction of I by the homolytic cleavage of the C(sp2)–C(sp2) bond to radical II, the addition of the isobutyronitrile radical, and

1,2-Difluoroethylene (HFO-1132): synthesis and chemistry

• Liubov V. Sokolenko,
• Taras M. Sokolenko and
• Yurii L. Yagupolskii

Beilstein J. Org. Chem. 2024, 20, 1955–1966, doi:10.3762/bjoc.20.171

• magnesium [50][51] to form the desired 1,2-difluoroethylene as a mixture of E- and Z-isomers, which were separated by fractional distillation (boiling point: −53.1 °C for (E)-HFO-1132 and −26.0 °C for (Z)-HFO-1132 [47]). In patent literature, a variety of synthetic routes to HFO-1132 starting from other

• cis-isomer decreases, i.e., the cis-isomer of 1,2-difluoroethylene is thermodynamically favored [47]. Deuteration The stereospecific reaction of (E/Z)-1,2-difluoroethylene with a 1–2 M solution of NaOD in D2O (90–120 °C, 2 d) led to the formation of CDF=CDF with high isotopic purity (Scheme 8) [76][77

• ]. Additionally, when the reaction was performed using DMSO-d6 (or CD3CN) and CH3ONa, H/D exchange occurred already at ambient temperature (25 °C, 20 h) [78]. The formation of CDF=CDF was confirmed by NMR spectroscopy, namely by the change of signal multiplicity in the 19F NMR spectra of E- and Z-isomers of 1,2

Regioselective alkylation of a versatile indazole: Electrophile scope and mechanistic insights from density functional theory calculations

• Pengcheng Lu,
• Luis Juarez,
• Paul A. Wiget,
• Weihe Zhang,
• Krishnan Raman and
• Pravin L. Kotian

Beilstein J. Org. Chem. 2024, 20, 1940–1954, doi:10.3762/bjoc.20.170

• similar to 6. They observed high N1-selectivity using NaH in THF with pentyl bromide and electron-deficient indazoles, postulating a coordination of the indazole N2-atom and an electron-rich oxygen atom in a C-3 substituent with the Na+ cation from NaH. Under anhydrous conditions the yields ranged from 44

• % at room temperature to 89% when warmed to 50 °C. No information was provided to justify any N2-selectivity or the lack thereof. Should an N2–Cs+–O ion pair exist, this could reasonably account for all the reported results presented herein (vide infra). Additionally, using Cs2CO3 in dioxane provided

• S1 in Supporting Information File 1. Stoichiometric manipulation of 12 to 6 in DMF at 90 °C provided the N1-substituted product P1 in 52–60% yields. The yields of P1 formation were largely unaffected in DMF with temperatures ranging from room temperature to 110 °C. Varying the equivalents of Cs2CO3

A new platform for the synthesis of diketopyrrolopyrrole derivatives via nucleophilic aromatic substitution reactions

• Vitor A. S. Almodovar and
• Augusto C. Tomé

Beilstein J. Org. Chem. 2024, 20, 1933–1939, doi:10.3762/bjoc.20.169

• Vitor A. S. Almodovar Augusto C. Tome LAQV-REQUIMTE, Department of Chemistry, University of Aveiro, 3810-193 Aveiro, Portugal 10.3762/bjoc.20.169 Abstract Diketopyrrolopyrroles (DPPs) are a versatile group of dyes and pigments with valuable optoelectronic properties. In this work we report the

• , 120 °C, 2 h) resulted in very low yields (6–16%) for the formation of N,N’-bis(pentafluorobenzyl)-DPP derivatives [36]. Changing the base to NaH and performing the reaction at a lower temperature, enabled to obtain DPP 2 in a reasonable yield (61%) and allowed us to use it as a starting material for

• chromatography (TLC) was carried out on precoated sheets with silica gel (Merck 60, 0.2 mm thick). Preparative TLC was carried out on 20 cm × 20 cm glass plates precoated with a layer of silica gel 60 (0.5 mm thick) and activated in an oven at 100 °C for 12 h. Melting points were determined with a Büchi B-540

Negishi-coupling-enabled synthesis of α-heteroaryl-α-amino acid building blocks for DNA-encoded chemical library applications

• Matteo Gasparetto,
• Balázs Fődi and
• Gellért Sipos

Beilstein J. Org. Chem. 2024, 20, 1922–1932, doi:10.3762/bjoc.20.168

• access to compounds featuring C(sp2)–C(sp3) bonds. However, the general view is that this transformation is less reliable than its orthogonal counterpart, the Suzuki reaction. Recent years have seen significant developments in Negishi reaction methodologies [34][35][36][37][38][39]. In particular

Solvent-dependent chemoselective synthesis of different isoquinolinones mediated by the hypervalent iodine(III) reagent PISA

• Ze-Nan Hu,
• Yan-Hui Wang,
• Jia-Bing Wu,
• Ze Chen,
• Dou Hong and
• Chi Zhang

Beilstein J. Org. Chem. 2024, 20, 1914–1921, doi:10.3762/bjoc.20.167

• isoquinolinone derivatives. The method provides highly chemoselective access to 3- or 4-substituted isoquinolinone derivatives by reacting o-alkenylbenzamide derivatives with PISA in either acetonitrile or wet hexafluoro-2-isopropanol. Keywords: annulation; C–H amination; hypervalent iodine reagent; iodine(III

• zwitterionic water-soluble hypervalent iodine reagent (phenyliodonio)sulfamate (PISA). In water, PISA is strongly acidic, and the pH value can reach 2.05 in a saturated aqueous solution. With PISA, various indoles have been synthesized via C–H amination of 2-alkenylanilines involving an aryl migration

• , isopropyl, cyclopropyl, phenyl, or hydrogen, respectively, the intramolecular amination smoothly gave the corresponding 4-substituted isoquinolinone products 2b,c,d–f in 51–94% yield. Notably, when 1c was used as the substrate, the cycloisomerization product 2c' was observed in 31% yield besides 2c in 51

Novel oxidative routes to N-arylpyridoindazolium salts

• Oleg A. Levitskiy,
• Yuri K. Grishin and
• Tatiana V. Magdesieva

Beilstein J. Org. Chem. 2024, 20, 1906–1913, doi:10.3762/bjoc.20.166

• amount (5%) of the N,N’-diaryldihydrophenazine radical cation that is the byproduct corresponding to the intermolecular oxidative C–N coupling of the diarylamine A1 was detected in the reaction mixture. This emphasizes that the both processes are of the same nature and proceed through the same

• intermediate (i.e., the diarylamines’ radical cation) and indicates the dominance of the intramolecular cyclization over the intermolecular C–N coupling process. Oxidation of diarylamines in the presence of an excess of trifluoroacetic acid gave no targeted pyridoindazolium salts, whereas the amount of

• previous mechanistic study [20][21] which revealed that the intermolecular C–N and C–C couplings are disfavored in case of the diarylamines with two electron-deficient phenyl rings. To our surprise, the procedure did not work in the case of amine A3: only traces of pyridoindazolium salt S3 were detected in

Access to 2-oxoazetidine-3-carboxylic acid derivatives via thermal microwave-assisted Wolff rearrangement of 3-diazotetramic acids in the presence of nucleophiles

• Ivan Lyutin,
• Vasilisa Krivovicheva,
• Grigory Kantin and
• Dmitry Dar’in

Beilstein J. Org. Chem. 2024, 20, 1894–1899, doi:10.3762/bjoc.20.164

• cyclization [15][16]. Additionally, the manganese(III)-promoted cyclization of N-alkenyl malonamides [17][18] and the Cu(I)-catalyzed reaction of propiolic acid derivatives with nitrones (Kinugasa reaction) [19][20][21] should also be mentioned, as well as intramolecular C–H insertion using

• tested in a previous study [3]. The reaction requires rather severe heating under microwave irradiation (200 °C, chlorobenzene, sealed vial), ensuring complete conversion of the diazo compound in a rather short time. Initial experiments using p-anisidine as a nucleophile showed that the target β-lactam

• derivative 3a could be obtained in high yield (83%) after simple chromatographic separation of the reaction mixture (Scheme 2). When the synthesis was carried out using conventional heating in 1,2-dichlorobenzene (200 °C, 1 h), product 3a was obtained in slightly lower yield (75%), so further experiments

The Groebke–Blackburn–Bienaymé reaction in its maturity: innovation and improvements since its 21st birthday (2019–2023)

• Cristina Martini,
• Muhammad Idham Darussalam Mardjan and
• Andrea Basso

Beilstein J. Org. Chem. 2024, 20, 1839–1879, doi:10.3762/bjoc.20.162

• synthesis (DOS) where a single methodology should generate diverse scaffolds. This comprehensive review focuses on all these aspects, and has been divided into five chapters, describing, respectively: a) efforts to develop new and milder reaction conditions; b) the use of new building blocks; c) the

• on different substrates, the conditions were similar: 20 mol % of the catalyst, ethanol as solvent at 80 °C in the first case, 30 mol % of catalyst, ethylene glycol at 90 °C in the second case; however, a striking difference appears when the reaction was carried out in the absence of silver catalyst

• , reported that, by using hexafluoroisopropanol (HFIP) as the solvent, GBB adducts derived from glycal aldehydes could be isolated without additional catalysts in a few hours at 25–50 °C [10]. In this case, however, the role of the solvent as a Brønsted acid cannot be ruled out (this article will be

A facile three-component route to powerful 5-aryldeazaalloxazine photocatalysts

• Ivana Weisheitelová,
• Radek Cibulka,
• Marek Sikorski and
• Tetiana Pavlovska

Beilstein J. Org. Chem. 2024, 20, 1831–1838, doi:10.3762/bjoc.20.161

• bearing electron-donating or halogen groups. This practical method is characterised by atom economy and offers a direct route to the introduction of an aryl moiety into the C(5)-position of deazaalloxazines, thereby generating novel catalysts for photoredox catalysis without the need for subsequent

• (All) and also 5-deazaflavins (dFl) and 5-deazaalloxazines (dAll), where the N(5) atom of the isoalloxazine/alloxazine core is replaced by a C–H moiety (Figure 1A). In particular, 5-deazaflavins have generated considerable interest from scientists to study flavin-catalysed reactions in enzymatic and

• -deazaflavins [11][12][13]. Recently, it has been discovered that both 5-deazaflavins 1 and 5-deazaalloxazines 2, which have an aryl substituent in position C(5), form stable radicals that act as powerful reductive photocatalysts with a reducing power comparable to that of lithium [E*(1/1•) = −3.3 V vs SCE

Hetero-polycyclic aromatic systems: A data-driven investigation of structure–property relationships

• Sabyasachi Chakraborty,
• Eduardo Mayo Yanes and
• Renana Gershoni-Poranne

Beilstein J. Org. Chem. 2024, 20, 1817–1830, doi:10.3762/bjoc.20.160

• structural resolution: a) global properties, b) atomic composition, and c) building block composition. At each of these levels, we analyzed the data according to various structural features, to elucidate the underlying structure–property relationships and delineate clear principles that can aid in rational

• separated and colored by the longest L for: A) all 9-ring molecules; B) all 9-ring molecules that do not have an antiaromatic moiety in the longest linear stretch; C) all 9-ring molecules that do not contain any antiaromatic moiety. The KDEs are normalized such that the area under each curve is 1

• . Distributions of molecular properties for 4n and (4n + 2) π-electron count systems, divided by the number of rings for: A) HOMO and LUMO energies and B) Gaps. Stacked histograms showing the prevalence of the different heteroatoms across different areas of the property space, for A) HOMO, B) LUMO, C) Gap, D) AIP

Discovery of antimicrobial peptides clostrisin and cellulosin from Clostridium: insights into their structures, co-localized biosynthetic gene clusters, and antibiotic activity

• Moisés Alejandro Alejo Hernandez,
• Katia Pamela Villavicencio Sánchez,
• Rosendo Sánchez Morales,
• Karla Georgina Hernández-Magro Gil,
• David Silverio Moreno-Gutiérrez,
• Eddie Guillermo Sanchez-Rueda,
• Yanet Teresa-Cruz,
• Brian Choi,
• Armando Hernández Garcia,
• Alba Romero-Rodríguez,
• Oscar Juárez,
• Siseth Martínez-Caballero,
• Mario Figueroa and
• Corina-Diana Ceapă

Beilstein J. Org. Chem. 2024, 20, 1800–1816, doi:10.3762/bjoc.20.159

• filter as their presence is not needed for biosynthesis, albeit it is for resistance. As a result, the C. cellulovorans 743 clusters were chosen because they were thought to be complete, novel, and most interesting, primarily due to the presence of two different, apparently independent operons, each with

• cluster of C. cellulovorans 743, clostrisin and cellulosin were compared with known lanthipeptides, generating a similarity network made using the percent identity between the precursor peptides from all experimentally characterized lanthipeptides to date (Figure 3A). We found it noteworthy to examine the

• function–structure relationships and how they impact biological activity. Since we have not found evidence of horizontal transfer of the cloA1 and cloA2 gene clusters, it is an interesting speculation that they could constitute the origin of this family and that, by duplicating one of these clusters, C

Chiral bifunctional sulfide-catalyzed enantioselective bromolactonizations of α- and β-substituted 5-hexenoic acids

• Sao Sumida,
• Ken Okuno,
• Taiki Mori,
• Yasuaki Furuya and
• Seiji Shirakawa

Beilstein J. Org. Chem. 2024, 20, 1794–1799, doi:10.3762/bjoc.20.158

• catalysts in the asymmetric bromolactonization of 5-hexenoic acid derivatives without additional substituents on the carbon–carbon double bond (Scheme 2). The catalytic asymmetric bromolactonization of model substrate 2a with N-bromophthalimide (NBP) was conducted at −78 °C for 24 hours using chiral